I made sure I had mastered my sailing prior to taking on the Boss Battle, as well as having about a level 10 or so VooDoo Staff for taking on the Navy Soldiers at the start of the Boss Battle... That way I didn't have to be so picky on my crew, I done it with just some random eager pirates on Abassa server the first time I done it. You can get another person to sail for you, but I would think you would want to sail the Black Pearl yourself and win for your quest.
Best of luck to you mate.
Larence Tuppington